


I Want To Hold Your Hand

by buttercreambeans



Category: Supernatural
Genre: 1960s, Alcohol, Alternate Universe, Alternate Universe - 1960s, Alternate Universe- No Supernatural, Angst and Fluff and Smut, Best Friends, Castiel Is Bi, Castiel is a Tease, Dean Being Dean, Dean Being an Idiot, Drugs, Eventual Relationships, Eventual Romance, Eventual Smut, F/M, Falling In Love, Fluff, Gay Rights, Graffiti, Hate to Love, Jealous Dean, Jukeboxes, Leather Jackets, Lesbian Charlie, Love Confessions, Love Letters, Matchmaker Charlie, Other Additional Tags to Be Added, Popular Dean, Protective Dean Winchester, Protests, Romance, Sam Being Sam, Sam Winchester is a Little Shit, Segregation, Teen Romance
Language: English
Status: In-Progress
Published: 2017-01-01
Updated: 2017-01-31
Packaged: 2018-09-13 12:02:54
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 6,272
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9122770
Author URL: https://archiveofourown.org/users/buttercreambeans/pseuds/buttercreambeans
Summary: The year is 1964. When you are invited to football captain - Dean Winchester's party, things couldn't have gone more wrong. What started out as a passion of hating the older Winchester develops into something else.





	1. Welcome to the '60s!

**Author's Note:**

> Hey y'all! Thanks for choosing to read my story! I hope you enjoy and please leave some feedback in the comments! Thanks again. :)
> 
> Also, Happy New Years! 
> 
> Title is inspired by The Beatles': "I Want To Hold Your Hand"

You shook the spray can of white paint. The can rattled throughout the empty alleyway. You hummed along to the music that played from your portable radio, which you happily got for your birthday. You began spraying paint onto the plain, red brick wall. 

"Hey, (Y/N)!" 

You turned your head towards the sound of the voice. 

"Oh, hey, Cas!" You shouted back, continuing to spray paint onto the wall ahead of you. "What's up?"

"You ridin' with us to school or not?" He asked. 

"Yeah. Just gimme a sec." You sighed disappointingly, tossing the can of spray paint back in your backpack. You grabbed your radio, pulling down the antenna. 

You jogged out of the alleyway and hopped into the backseat of Cas' new 1964 Cadillac Fleetwood.

"Sweet ride." You chuckled. Charlie, your best friend, sat in the front seat next to Cas. 

"Bet this is nothing compared to Mr. Popular's, right, (Y/N)?" Cas winked at you through the rearview mirror.

"Oh, quit it." You grumbled. "He's only got that hot ride 'cause his dad's the biggest mechanic in town." 

"Hey, are you two going to his party by the way?" Cas asked, his ocean eyes bouncing between you and Charlie.

"Dean's party? We didn't get an invitation." You said, furrowing your eyebrows.

"Well, his little brother...I think his name is Sam - he gave me this," He fished out a small card from the pocket of his cadet sweater. "...if I were to go, I wouldn't wanna be alone."

"But Dean's gonna be there, so you won't be alone." Charlie began making kissy faces at Cas. 

"Gross." Cas laughed. "He's fine as wine, but...I believe our dear friend has called dibs on him." 

"Ugh, he probably isn't even gonna notice me. He's basically the Elvis Presley of the school." You groaned, throwing your head back. 

"Speak of the devil..." Cas muttered, gesturing out his rolled down, tinted window. You followed his gaze, which led to none other than Dean Winchester, football captain and class president.

Charlie sighed, rolling her eyes as the car came to a stop.

Your eyes wandered over his sandy, dark blonde hair. His pink and sinful lips that looked deliciously plump. 

"He's lookin' sharp, ain't he, (Y/N)?" Cas smirked at you, hopping out of the driver's seat. You followed suit, slamming the backseat door behind you. "Careful!" 

"Whoops, sorry." Your eyes drifted down to Charlie's new, white gogo boots. "You gonna hook me up with some of those, girl?"

"You know I will." She chuckled, throwing an arm around your shoulders as you were about to enter Jensen High. "Cas, we meetin' later for milkshakes down at Jody's?"

Cas nodded, giving you both a two-finger salute as he ran to the boys' locker rooms, which were behind the school. You nervously smoothed down your polka-dotted poodle skirt and zipped up your cropped leather jacket as you slid through the double doors that led to the main hallway of the school.

Immediately, the smell of sweat and hairspray clogged your nostrils as you and Charlie pushed through the swarms of teenagers. 

"Do you think Mr. Crowley ever thought of renovating this hell hole?" You said to Charlie, who was busy flirting with some girl. You rolled your eyes with a smirk before taking long strides to your locker.

Your (E/C) wandered over the posters of The Beatles, LGBT rights, and pop art that covered the inside of your locker as you stuffed your backpack inside before you grabbed your books for your classes. You jumped when someone slammed your locker shut, nearly jamming your pinky finger.

"Hey! I wasn't-"

"Oh, I'm sorry." Lisa, one of the cheerleaders, cackled, twirling her hair around her finger. Her dark eyeshadow popped out from the rest of her bright outfit. Her black hair was pinned up, forming a beehive on the top of her head. Her blush was overdone, making your scoff. "You were in my way." 

You cursed under your breath as you walked away from her and your locker. "What a stuck-up." 

"I was looking for you." Charlie whined as she grabbed your arm, almost causing you to drop your books. 

"Same here. You were busy flirting with some chick." You teased her. "Isn't her name like Barbara Sinclair? New girl, right?"

"Yeah. She's hot." 

"A total babe, right, Charlie?" You nudged her ribcage with your elbow, chuckling as she grumbled.

The school bell rang. It's long and obnoxious ring echoed throughout the colorful hallway that you happily decorated. 

"I'll see you at third." You smiled at Charlie, giving her a brief hug before you padded your way down to your class.

* * *

 "Your assignments are due by the twenty first. Please do not turn them in late because I will not be accepting them." Your English teacher said, clearly uninterested in communicating with his students as he read a book.

You grabbed your books and scurried out of the classroom. Charlie was already waiting for you outside. You didn't know how she got out of class so early. Maybe because she didn't go to class at all. You smiled at her gratefully as she offered to hold your books for you, but you happily declined.

"No, Charlie. It's fine, it's only-"

You winced when you ran into a hard, yet soft, surface. Your books fell out of your hands and slid onto the floor. You looked up, your eyes widening.

"Well, hello, cherry." You locked eyes with one of Dean's friends. Benny Lafitte. 

"Oh, my, god. I'm sorry. I didn't mean to-"

"Shhh." Benny chuckled, glancing back at his friends. His eyes drifted towards Charlie, who scrunched up her face in disgust. "What's up, skag?"

"Hey, watch your mouth." Charlie snapped, stepping in front of you protectively.

"Why should I, you little queer?" He grunted, taking a step towards Charlie. 

"Don't underestimate me, you freaking flake." 

Benny huffed as he pushed Charlie out of the way, causing her to fall flat on her ass.

"You piece of shit!" You gasped, slapping Benny in the face. "Go to hell." 

You helped Charlie up, once she was back on her feet and she slapped Benny full force too.

"Eat shit." She growled, helping you pick your books off of the floor. The both of you briskly walked away, muttering a string of vulgarities under your breath.

"People need to learn to not mess with me." She mumbled, avoiding other students' gazes.

"Well, not a lot of the students here are gay friendly." You whispered.

"You should come and protest with me on Saturday. Cas might join." 

"I'll try. I have a huge test this week that I don't wanna fail. You know how tight the school is on grades." You came to a stop at your class.

"Thank you for earlier, (Y/N)." Charlie called out from over her shoulder as she began to walk away. "Peace out, bitches!"

You shook your head, chuckling at your best friend. You were about to step into class, but you were pulled back. When you turned to look, your breath hitched in your throat and your pupils dilated.

"Hey, (Y/N)." Standing behind you was Dean Winchester. He was wearing a green letterman jacket that complimented his beautiful eyes perfectly. The breast pocket of his jacket read, 'Jensen Cowboys', the school mascot. His hair was slicked back to the side, a hairstyle you've only seen him wear a few times. His bow legs were visible with his dark, blue jeans that he wore with a cheap leather belt.

Your eyes drifted down to your arm, where his large hand was wrapped around. He shyly pulled it back when he noticed your piercing gaze. 

"Dean." You faked a smile. Though you thought he was a hunk, you knew he was a major playboy. He was nice and a sweetheart, but you'd rather get your heart broken by someone worth it.

"Uh, look..." He started. "I just wanted to apologize for earlier. Y'know, with Benny and Charlie. I didn't-"

"You have no reason to apologize, Dean. That's Benny's fault, not yours. I'm sure your... _friend_ can stand up for himself." You tried to say politely. You were about to walk into class, but Dean stepped in front of you, his large frame blocking the doorway. "What now?"

"Lemme at least make it up to you." Dean pleaded with puppy eyes. 

"Fine, but make it quick." 

Dean slid his hand into the pocket of his letterman jacket, handing you a small card that was identical to the one Cas showed you earlier. 

"I'm having a house party tomorrow. Cas might be coming too. Bring a friend if you want 'cause, " Dean chuckled. "...it's gonna be a blast." 

"Okayyy..."  You said awkwardly, reading the messy words on the invitation that were clearly written by him. The address and the details to the party were all there.

"Sorry again." He smiled at you, flashing his pearly whites before leaving in a hurry.

You walked into class right before the bell rang, taking a seat at your table. You jumped when someone suddenly sat in the chair next to you, but that feeling was soon replaced with relief when you saw that it was only Cas.

But something was wrong.

"Hey." You smiled at him. He smiled back, but the smile did not reach his eyes. "Hey, what's wrong? Did coach go all ape on you again?"

"You could say that." He mumbled sadly.

"Cas?"

"I got...kicked off..." He swallowed thickly. "...the team."

"Oh, no."

"I decided that I was done hiding who I am. I wanted to come out to the team. 'Say I was bisexual and get it over with, but...Coach Cain heard me talk to Dean about it. I didn't know he was homophobic."

"Well, he's a fucking idiot." You said in a low whisper, patting Cas' thigh for assurance. "You're too good for that team anyways."

"Thanks." He sighed, smiling with appreciation.

* * *

 Before you knew it, it was the end of the school day. You strode out the front doors with Cas and Charlie, humming to a new Beatles song.

Out by the marquee - that you also happily decorated with your spray paint - was Dean and the football team. He glanced in your direction and once he saw you, he waved, a football in his hand.

You didn't wave back. However, you smiled. But everyone and their cat knew how forced that smile was. 

Cas scoffed. "I hate school." He said, unlocking the doors to his car. "Hop in."

"To Jody's?" Charlie asked with hope.

"To Jody's." He repeated, turning on the engine.

"So, I take it you're not going to his party anymore, Cas?" You probed, taking out your sunglasses from the front pocket of your backpack as he pulled out of the parking lot.

"I would, but...Benny and his fucking friends are gonna be there."

Charlie scoffed. "Yeah, and they're a bunch of damn dicks." 

"Dean invited me." 

"Benny was - he what?!" She practically screamed, eyes going wide. 

"Jesus!" You gasped, putting on your shades. "Yes, he did! And keep it down!"

"It's not like he's gonna hear me anyways," Charlie muttered. "But he invited you?! My best friend... _oh, and the football captain. Together at last._ High school sweethearts. I can totally see a future happening in my crystal ball." She sighed dreamily.

You reached over the bench seat and slapped her on the back of her head, her red hair bounced as she went to rub the area.

"Ow." She chuckled.

* * *

 A small jingle of a bell rang throughout the diner as you, Charlie, and Cas entered Jody's Diner. The most famous restaurant for burgers and fries in the county.

"Hey, kiddos." Jody grinned at you as she went to assist a table, holding a tray of milkshakes for them. She came back empty-handed, but made you take a seat at the barstools.

"Jody. Looking sharp, today," You chuckled at her as she went to scribble something on the palm of her hand.

"The usual?" She pointed at the three of you. You all nodded with big smiles as she scurried to get your orders ready.

The door behind you swung open and you stifled a loud groan. Dean and his group of friends.

Of course.

Lisa was practically glued to Dean's side, Benny - thankfully - wasn't there, but he was with his cousin Jo, and her friend, Ash. You knew Jo from kindergarten, but you haven't really talked. Sam, his younger brother, was there, but it looked like he didn't belong. Though, you noticed Sam was with Cas' older brother, Gabriel, the school prankster. A cigarette was placed between Dean's lips, making you roll your eyes. 

"Here y'all go." Jody said, placing a chocolate milkshake in front of you, a vanilla one in front of Charlie, and a strawberry one for Cas. Jody followed your gaze, rolling her eyes as she placed her hands on her hips. "Those friends of yours are always trouble. Especially the cute blonde one."

"They're not our friends." Cas scoffed, sipping his milkshake. 

"Well, let me go get your onion rings and fries before I go help those kiddos." She sighed, walking back into the kitchen.

Dean and his group slid into an empty booth, already causing a ruckus.

"Did you hear about the protest down by Riverside?" Cas piped up, glancing at you and Charlie. "Shit got out of hand. The protestors were arrested."

"It's stupid. People are always talkin' about voicing your own opinion, and here we are, _voicing our own opinion,_ but we get punished for it." You sighed, gesturing to the small TV that hung in the corner of the wall. 

"I'm still going to the protest at the mayor's house on Saturday for gay and women's rights," Charlie said with a pout. "I really don't care if I get arrested."

"Right on." You nodded. "Just know that I'm not rich enough to bail you out, sweetie."

Jody slid a red basket full of fries and onion rings down your table, then winked before she went to help Dean's booth.

"Time to pig out." Cas laughed, snatching a fry from the basket. 

"Hey, is your tattoo shop open tomorrow?" You nudged Charlie.

"My tattoo shop? Girl, I don't even have one." She snorted. 

"Oh, you know what I mean." You raised a brow. "I heard about your whole homemade tattoo thing. Dorothy, you know the girl who supposedly has a thing for you, told me. Hook me up." 

"Fine." She mumbled. "But it's gonna hurt."

"I'm not a wuss." While you and Charlie were busy talking, it was not until a few minutes later than you noticed Cas was talking to someone. You looked down the table to see him talking to Dean. You slapped Charlie's thigh, bobbing your head towards the two.

"...look, I feel awful that you got kicked off the team." Dean sighed. "...you were a valuable player. But I can't do nothing about it. Coach Cain calls all the shots."

"I don't even care anymore, Dean."

"Maybe you shouldn't have...told the team."

"Yeah," Cas huffed, tossing an onion ring into his mouth. "And now the whole school knows."

"I get why you did it, they're just a bunch of dicks. Sorry, bud." He smiled sadly, patting Cas' back before he returned to his table.

"How nice of him." You mumbled, hearing  the teasing giggles of his friends once he sat down.

"Is he still dating Lisa?" Charlie said in a low voice.

"They broke up a while ago. Ash caught her with this guy, Andy." 

 "And yet they're still friends?" 

"At least that's what Lisa thinks."

* * *

 

You collapsed onto your bed, moaning. You buried your face into your white pillow, drowning yourself in your own scent. Charlie slept in the room next to you. You lived with her and her mom, since your parents were divorced. But your dad was serving a ten year term in prison and your mom worked abroad.

Your vintage record player played Elvis Presley in the background, lulling you to sleep.

You slipped your hand into the pocket of your leather jacket, looking at the card Dean gave you as you lay down. You huffed as you looked at his writing, then turned the card over. There, in messy red ink, was his number. 

_Call me. - D.W. ♡_

You ran a hand down your face, a smile tugging at the corners of your lips.

"What did I get myself into?"

**Notes for the Chapter:**

> So, recently, I just ended one of my main fics, Only Fools. I am now introducing a new one, which is I Want To Hold Your Hand. It's heavily inspired by the events of the 60s and all that. Many more chapters to come!
> 
> Thanks for reading! Please leave a kudos, comment, or both!


	2. Blue Velvet

**Notes for the Chapter:**

> Read end notes!

It was Saturday. The day of Dean Winchester's famous house party. You wore a blue velvet miniskirt and a cropped, leather tank top. Your hair was done in a bombshell, which Charlie's mom happily styled for you since she was a hairdresser. 

You borrowed Charlie's white gogo boots that perfectly complimented your flower choker. You had tried your best to look hip, but Charlie said you ended up looking like a flower child - which in your opinion, was a compliment. Cas agreed to go with the two of you, but only because his brother, Gabe, would be there. You decided to meet with him there later, as Charlie's mom was going to drop you two off.

The door to your room creaked open. There, in red boots and a floral dress, stood Charlie with flowers in her red hair.

"Hey, gorgeous." She smiled at you. 

"Very funny." You blushed, grabbing your purse before making your way outside with her.

Charlie's mom waited in her car, honking at the two of you to hurry up since she had customers to get back to.

"You ready to party?" Charlie asked you.

"Born ready." You winked. 

* * *

 Instantly, the sound of pop rock music filled the busy streets by Dean's house. Los Angeles, noisy as ever. 

"You girls be safe, okay?" Charlie's mom said firmly. "Make sure no boys reach up that short skirt, (Y/N)." She glared at you with a funny face.

"Yes, ma'am." You chuckled, shutting the door of her car lightly. 

You and Charlie approached Dean's house quickly, smiles plastered on your faces. She raised a hand to knock on the door, but it swung open, nearly knocking her over. 

 A drunk Gabriel stood there with an empty Coca-Cola can in his hand. 

"Hey, chick-a-dees." He slurred, opening the door wider for the two of you. "Come on in. You've been missing out."

You and Charlie exchanged glances, shrugging before you stepped inside Dean's house. 

The lights were out, except for the disco mirror ball in the center of the living room. Girls and guys danced together and grinded against each other. You awkwardly stood by the kitchen island that was covered in beer and coke cans. 

"Hey!" You turned around, face to face with Dean. "I'm glad you could come!" He said over the loud music.

"Well, I couldn't leave you hanging!" You replied back, self-consciously tucking a strand of hair behind your ear.

"Want one?" Dean handed you a can of beer. "It's for free! Take as much as you want!" He winked.

"I will!" You smiled, opening the can. You took a sip, sighing at the refreshing burn at the back of your throat.

"I gotta go talk to some people. Have some fun! I'll find you later!" He exclaimed, squeezing your shoulder before he left. You blushed a deep red as you dipped your head and began to drink your beer.

"(Y/N)!" You turned around to see Cas. 

Drunk Cas. Maybe even a little high.

"Dude, are you alright?" You chuckled, putting your hands on both of his shoulders once he stumbled towards you.

"So awesome. I'm having a blast! You?" He slurred flirtatiously.

"I'm fine!" You grinned. "Hey, where's Charlie?"

"I thought she was with you!"

"No, she must've went to find you!"

"She's probably making out with the one chick. What's her face...Maya? Debbie?"

"Barbara, I think." You replied. 

"Well, if Charlie's getting some, then I have to get some!" Cas brushed past you, reeking of Marijuana. You shook your head, continuing to gulp down your drink as you waited for Dean to return.

* * *

"Hey, I'm back!" Dean smiled, running a hand down your arm as he moved to stand in front of you.

"Cool, you have any more?" You asked, gesturing to the three empty bottles of beer next to you.

"You're not drunk yet?"

"I mean - I don't feel that - that buzz, you know? Maybe something stronger could do it."

"I got you." Dean chuckled as he went to go look in his full fridge. "Here! I was gonna save it for a special occasion!"

"Well, this is pretty special." You grinned, taking the bottle from him.

"Would you like-"

You unscrewed the cap off the bottle, chugging it down quickly. You sighed in relief, wiping the drops of alcohol off your chin.

"Damn, (Y/L/N)." Dean bit his bottom lip. 

"This'll do! Thanks, D." 

"No problem. You wanna dance?" He asked, jerking his head towards the middle of the living room where the disco ball was.

"I don't dance, Winchester." You replied breathlessly. "I don't do crowds either!"

Dean glanced behind him. "C'mon, follow me."

"Uh, to where?"

"You said you didn't like crowds. Well, we can go up to my room. You know, hang around."

"Hang around, really, Dean?" You scoffed. "No thanks."

"Fine. The roof. C'mon. Let's stargaze or whatever."

"I can go by myself. It's your party and you're the host. You should be down here with your friends."

"No. No, it's cool." He insisted. "I wanna join you anyways."

You blushed, chuckling with a grin. "Lead the way."

* * *

 Dean held his bedroom window open as you crawled out onto the roof. You did the same once you were through. You shut the window behind Dean as he walked to the edge of the roof and sat down. 

You sat next to him as he handed you another bottle of whiskey. 

"Trying to get me drunk?" You joked, nudging his shoulder with yours. He chuckled deeply, shaking his head at you. 

"Just a little." He answered, opening the bottle for you. As you took it from Dean, he reached into the back pocket of his jeans, grabbing a single cigarette.

"Those can kill you, you know." You said, feeling the burn of alcohol at the back of your throat.

"So can drinking." He smiled, lighting the cigarette. You watched closely as he put the fag between his lips, puffing out smoke. He tapped the top of his cigarette as he took it from between his lips and then put it back.

Dean stared at the stars as you stared at him while drinking. The night sky illuminated his perfect face. The way his hopeful, lively green eyes bounced back and forth from the sky to his shoes made you sigh. You tugged down your skirt as it hiked up your thighs, feeling a bit conscious as Dean glanced at you. 

It was when you caught each other's gazes that you felt heat pool between your thighs. Dean's green eyes roamed over your face almost longingly. 

Was he - was he going to kiss you? 

"What are you-" Dean quickly pulled out the cigarette between his lips and threw it below him, then cradled the back of your head as he pressed his lips against yours.

You stiffened as his lips molded against yours, but you soon relaxed when Dean's other hand drifted into your hair, tugging.

You moaned as his tongue slid into your mouth. Your thumb brushed against his cheek, following the smatter of freckles. 

"Dean..." You breathed out, pulling away. "I..."

"I need you. I want you so bad." He moaned, looking at you with pleading eyes. You gulped as you saw the tent in his pants, muttering a small 'okay'.

He groaned as you ran your fingers through his short, spiky blonde hair. You pulled away, gasping for breath.

"Did I - did I do something?" He asked worriedly, placing his hand on your arm.

"No - I just..." You inhaled sharply. "We just can't - I can't. It's - you're amazing but I shouldn't do this."

"Why not?" He probed.

"I...it doesn't matter - plus, you're with Lisa. I'm not like those other girls. I don't -"

Dean huffed. "Who said I was with Lisa?"

"It's still a 'no', Dean." You said firmly, narrowing your eyes at him.

"You sure?"

"Very sure."

* * *

 

Dean slammed his bedroom window behind him before he pushed you up against the wall. You moaned as he sucked and nipped at your neck, right below your jaw.

"Dean..." You panted, shutting your eyes as he unzipped the back of your top, exposing your bra. 

"Fuck." He chuckled lowly, shrugging off his red and black checkered flannel. You took the chance to push him onto his bed, hearing it squeak loudly as he landed on it with a muffled thud.

He propped himself up on his elbows as you crawled on top of him, straddling him. He looked at you with wide, hungry eyes, breathing quickly as you unclasped your bra and threw it across the room.

"Yeah," Dean moaned, cupping your exposed breasts. He flipped the both of you over, so that you were underneath him, writhing in arousal. He pushed up your skirt, causing it to bunch up around your hips. Dean's eyes flickered up to yours as he licked his lips. "Dirty girl." 

You chuckled, shutting your eyes with a smirk as Dean got to his knees and placed his warm mouth on your wet core. 

"Oh, my god - Dean, yes." You moaned, grabbing a fistful of Dean's hair. He grunted when you tugged on his dark blonde strands as his mouth sucked on your clit. You bit back a scream when he dipped two fingers inside you, beginning to pump in and out as his mouth continued to work on your swollen clit.

"Mmm..." You gasped loudly, pushing Dean's head closer to your warm and wet core.

"You close?" He murmured huskily.

"Yes - oh - yes." You whispered. Your jaw fell open as he began to work faster, till all you saw was stars. You called out his name, thighs quivering and slick with your juices.

"So damn hot." He chuckled. "On your knees." He said with a deep voice. You pulled off your skirt and fell to your knees, looking up at Dean innocently. 

"Mmm, what do you want me to do?" You slurred flirtatiously as Dean got rid of his jeans and underwear, revealing his long and thick cock.

"I need you so fucking much, (Y/N)." He groaned as you wrapped your lips around the tip of his head, bobbing your head as you sucked him. Soft moans escaped his lips as you placed a hand on his thigh to steady yourself while you went faster. "Fuck, yes. God - oh..."

Dean threw his head back, screwing his eyes shut. His dirty moans made you even wetter. Your middle drifted down between your legs, dipping into your wet folds as you bobbed your head up and down on Dean's cock.

"Oh, yeah, (Y/N)." He mumbled, giving little thrusts into your mouth. "I'm gonna - oh, fuck, I'm gonna-"

A strained moan escaped for Dean's lips as he came in your mouth, you moaning, feeling him hit the back of your throat as he slowly and roughly pulled out. 

"We should've done this sooner." You giggled, getting to your feet.

"God, yes." He sighed. "Get on the bed." 

You slowly sat on the edge of his unmade bed, spreading your legs as Dean positioned himself in front of your entrance.

Your jaw fell open and your eyes rolled to the back of your head as he slowly pushed himself inside you, nearly filling you up with his large length once he was fully inside you.

"Dean, oh-"

"Does it hurt?" He whispered as he thrusted gently.

"No...no, keep going." You gave Dean's arm an affectionate pat as you smiled forcefully at him. He placed his hands on your hips carefully, rocking back and forth on his heels as he begun thrusting into you once more.

It wasn't hot. No, nothing about this was hot or sexy or romantic. It was desperate and messy. It consisted of sweaty and tangled limbs and awkward laughs. Heads bumped and apologies escaped one another's lips instead of moans. This wasn't sexy, god, it was anything but that.

But as Dean shut his eyes and buried his head in the crook of your neck, you felt bliss as he pushed deeper inside you. His hot breaths lingered on your bare shoulder, your chest heaving. Maybe you wouldn't remember this, Dean thought. Though, he did have a tiny crush on you ever since the second grade.

His hands drifted towards your back, where he ran them down your spine. His fingers memorizing the bumps down the center of your back as if it was the last time he ever will. Which may be the case.

Your breaths became more ragged as Dean moved at a faster pace, nearing you to the edge. You cried out his name, balling your hands into fists as you released your grip on his shoulders.

Dean followed after, whispering your name as he came. He stayed still for a while, resting his head on your shoulder as you clung to him.

"I'm gonna go clean myself up." He said, kissing your jaw before he padded over to his bathroom.

Your eyelids became heavy, sleep and drunkeness overcoming you. You laid down on Dean's bed, shutting your eyes. 

Dean came back with a frown on his face, seeing you fall asleep in his bed. Thoughts of staying up and talking to you filled his unrealistic mind. You probably wouldn't wanted to have talked to him anyways, he thought. He was just the football captain in the first place. He was no one special. Not smart enough, maybe not good enough.

He was just Dean Winchester.

And you were just (Y/N) (Y/L/N).

Dean didn't see that though. He saw a strong woman, independent and free, not afraid to express herself through art and protests and through her taste in music. You, with your cheap poodle skirts and thrift shop leather jackets and your untamed yet beautiful hair.

He saw someone who was maybe too good enough for him.

And so he slept next to you, pondering if he would ever get to do this again with you. Silently wishing he would, even though he knew that it would never.

Because you wouldn't like someone like him.

Right?

 

**Notes for the Chapter:**

> I'M SO SORRY THAT I DIDN'T UPDATE FOR LIKE 4 WEEKS! I've been super busy with other stuff that I had to push this aside for a second. However, usually I would post this on Sunday or Monday, so stay tuned! Thanks for sticking around and I'm sorry I wasn't able to get to this sooner. Deepest apologies everyone.
> 
> Find me on Instagram! @_winchester_united 
> 
> Thanks for reading! Please leave a kudos, comment, or both! ♡


	3. You've Lost That Loving Feeling

You groaned, massaging your temples as the morning light shone on your face. You stared at the ceiling in silence, before realization dawned over you slowly. This was not your room. 

Posters of Led Zeppelin, as well as other classic rock bands, and famous actors and athletes were plastered upon checkered walls.  
  
"What?" You gasped, briskly sitting up. The blue blanket that covered you slipped down, exposing your naked body. "Oh my..."  
  
You quietly turned your head over to the warm and sleeping body that lay next to you. His back muscles rippled as he inhaled and exhaled loudly, snoring. His spiky blonde-brown hair stuck up in many angles, creating an obvious bedhead.  
  
Then, you realized what had happened.  
  
Your eyes widened and you let out a shaky breath, covering your face with your hands. As you mentally face palmed yourself, Dean shifted so that he was now facing you. His eyes fluttered open; you were the first person he saw. He watched in confusion as you began groaning angrily - as if you had done something wrong.  
  
"Are you okay?" Dean asked suddenly. His voice was hoarse.  
  
"Dean!" You jumped in surprisement, falling off the bed along with your blanket. You hastily covered yourself up as Dean rushed to your side.  
  
"Hey, hey, what's wrong?" He began, giving you a small and comforting smile.  
  
"Um..." You struggled to form words. "I just wanted to - uh. Yesterday was a blast, but I - I think I should be going." You stammered. Hell, you had no idea what happened last night.  
  
Dean's soft grin fell as you shyed away from him, grabbing your scattered clothes. He leaned against his bed frame with a look of hurt as you hurriedly got dressed.  
  
You grabbed your bag then left the room without a word. You ran down the stairs, nearly running into the man himself, John Winchester.  
  
"(Y/N)?" He chuckled in surprisement. "What are you doing here?"  
  
You stifled a question, wondering how John knew your name.  
  
"Hi, Mr. Winchester, I just was - I went to drop off some assignments for Dean. He wasn't able to pick them up on Friday so I thought that he would want them." You lied plainly.  
  
John's face lit up. "Thank you, sweetheart. Here let me walk you to the door."  
  
Once John opened the door, you instantly stepped out and bid your goodbyes to Dean's father.  
  
Your face turned red when you realized that there was nobody to take you home.  
  
"Oh, damn it." You sighed, stomping your foot onto the sidewalk as you ran your hands through your hair in irritation.  
  
"Hey, (Y/L/N)!" You raised your eyebrows when Bela Talbot rolled up in front of the Winchester household. "Need a ride, hon?"

"Oh, definitely." You grinned, hopping in her convertible. "What brings you here?"

"Drugs." She chuckled. "Jo was down by the drive-in making deals."

"You'd expect the flower child to be good."

"Quite opposite really." She said in her thick English accent, chuckling softly. "Do you wanna bum a smoke?" She rummaged through her purse, taking out a box of Marlboro cigarettes. 

"No, I'm fine." You smiled thankfully, shaking your head. 

"Well," She grunted, lighting her cigarette gracefully. "Where do you want me to take you, sweetie? Home? Maybe a friend's house?"

"Castiel Novak's place, please." 

"The Heavens Tattoos?" She clarified, quirking a prominent brow. 

"Right on." 

* * *

 

"Thanks, Bela." You said, shutting the door of her convertible before she sped off. The neon lights of Heaven Tattoos illuminated your face and the grey sidewalk as you walked inside. "Mornin'," You greeted an employee, hanging your purse on the coat-hanger by the glass door.

"(Y/N)!" You perked up when a familiar, gruff voice greeted you. "What brings you here?" Cas walked through a set of white curtains, one hand held a curtain aside while the other held the needle used for inking people. 

"I need to tell you something."

"Well, yeah, me and Charlie were looking for you during the entire party last night! What happened? Jesus, (Y/N.)" He exploded, setting down the needle. He looked behind his shoulder, assuring his client that one of his employees will finish the rest of the art. "Gabe! Can you finish the rest of that customer's tattoo?"

"Yeah, I'll be there in a few." Gabriel answered, taping more posters onto the perfect, baby blue walls. 

"So, tell me..." Cas sighed, unrolling the sleeves of his tan trenchcoat. 

"Nice coat."

"Thank you." He smirked, before frowning. "Now, don't avoid the question. What. Happened. Last. Night?"

You bit the inside of your mouth almost hard enough to draw blood. You massaged your temples before shrugging. "I don't exactly remember."

"That's how buzzed you were?" His jaw hung open.

"I guess. I mean - I think I had at least two full bottles of whiskey."

"Please tell me that's not the only thing you remember."

"Well, Charlie went to find you, leaving me alone with Dean."

"And then?"

"I don't remember the rest." You rolled your eyes. "But this morning, I woke up in his room."

"Oh, jesus."

"Naked."

"(Y/N)!" He exclaimed, sounding like a parent who was scolding their child.

"That could mean anything other than - than sex!" You shouted, turning heads. "Sorry."

"Dude." Cas scoffed, scrunching his nose up. "Come on. You woke up naked. Next to him. You were drunk. And now you don't remember anything."

"Fuck, fuck, fuck." You mumbled, running a hand through your hair nervously.

"I mean," Cas chuckled. "It's not like it was your first time or anything."

You froze in your tracks.

"Right, (Y/N)?" 

You slowly turned around with pure horror on your face.

"Oh, shit." 

Soon, Cas' face was also covered in horror. "No way."

"I - I..." You began hyperventilating, causing Cas to rush to your side and help calm you down.

"I'm gonna get you home. You, Charlie, and I will have a calm conversation about this." He smiled. "Meaning that we'll all freak out over this."

You rolled your eyes at him before he grabbed his car keys and left the shop. You remembered that it used to be his dad's business, but his dad simply disappeared one day and couldn't be found. You always thought it was sad. But you also knew that Cas had lots of siblings, so he wasn't alone. 

* * *

 

 "You what?!" Charlie shouted almost insanely, jumping off the bed. "You did not..."

"I did."

"She did, Charlie." Cas laughed.

"OH MY - Seriously?!" She exclaimed. Her mother yelled from downstairs, telling her to quiet down. "You - You and Dean - you lost your-"

"-virginity to Dean Winchester?" Cas smirked. "She did."

"I was drunk. I don't even remember what happened exactly."

"But you remember enough to know what even happened." Charlie said.

"I woke up naked, Char. I think I know what that meant." 

"Hopefully the whole school doesn't." Cas sighed. "Imagine if he told everyone that you guys fucked - at his house party."

"He's not gonna tell everyone. That's not him."

 

**Notes for the Chapter:**

> Thanks for reading! Please leave a kudos , comment, or both!


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